Pyrazolone compound and process of making same.



Patented August 23, 1904.

UNITEDSTATES PATENT OFFICEQ MARTIN OVERLAOH, OF GREIZ, GERMANY, ASSIGNOR TO FARBWERKE VORM. MEISTER, LUOIUS & BRUNING, OF HOOHST-ON-THE-MAIN,GERMANY, A CORPORATION OF GERMANY.

PYRAZOLONE COMPOUND AND PROCES$ OF MAKING SAME.

SPECIFICATION forming part of Letters Patent No. 768,398, dated August23, 1904.

Application filed August 26, 1903. Serial No. 170,819- (Specimens) Toall whom it may concern:

Be it known that I, MARTIN OVERLAOI-I, M. D. a citizen of the Empire ofGermany, residing at Greiz, Germany, have invented certain new anduseful Improvements in Pywith bu'tylchloral.

It has been found that butylchlor'alhydrate, OH3.CHOl-OOl2-CH(OH)2,behaves differently toward L-dimethylamido-1--phenyl2:3-dimethyl-5-pyrazolone than does the chloralhydrate, for it readilyyields a beautifullycrystallized compound having the formula By clinicalexperiments it has been proved that the new compound is distinguishedbyvaluable therapeutic properties which do not belong to each componentby itself. The product is not asoporific,but an anodyne preparation.

The product may be obtained by heating together the two components assuch and subsequently recrystallizing the product of reaction fromdilute alcohol or benzene or by pouring together while hot solutions ofthe butylchloralhydrate and 4-dimethylamido-lphenyl2:3 dimethyl 5pyrazolone. When cold, the compound, having the melting-point 85 to 86centigrade, separates ascrystals.

Example I: One hundred and ninety-three to one hundred and ninety-fivegrams of butylchloralhydrate are melted on the waterbath with twohundred and thirty-one grams of4:-dimethylamido-l-phenyl-223-dimethyl-5- pyrazolone. When cold, thewhole solidifies to a crystalline mass, which is recrystallized frombenzene.

Example II: One hundred and ninety-three to one hundred and ninety-fivegrams of butylchloralhydrate are dissolved in about onebutylchloralhydrate and two hundred and V thirty one grams of 4cdimethylamido l phenyl-2z3-dimethyl-5-pyrazolone are heated with fourhundred grams of benzene until solution is effected and cooled. Thewhole is then filtered, washed with benzene or ligroine, and dried in avacuum.

The substance obtained by the above examples is a white powder ofyellowish tint having the melting-point of 85 to 86 centigrad'e. It issoluble with difiiculty in cold water, benzene, and ligroine, easilysoluble in alcohol and ether.

From clinical reports the new product has remarkable therapeuticproperties which do not belong to the two components as such. Theproduct is particularly valuable as anesthetic against the nerves of thebrain. No like result can be obtained with mere mechanical mixtures ofbutylchloralhydrate and 4:- dimethylamido-l-phenyl-2:3-olimethyl 5pyrazolone as with the chemical compound forming the subject of thisinvention, for the use of the former is accompanied by disagreeableby-efliects of the butylchloral, such as the feeling of giddiness.

Having now described my invention, what I claim is 1. The process hereindescribed of making a chemical compound which consists inheatingbutylchloralhydrate withi-dimethylamido-l-phenyl-2'z3-dimethyl-o-pyrazolone and purifying theproduct thus obtained by repound from butylchloralhydi'ate with &clil intestimony that I claim the foregoing asmethylaniiclo-l-phenyl-Q:3-(limethyl-5-pylazmy invention l have signedmy name in presolono, being a White powder of yellowish tint once of twosubscribing witnesses.

having the melting-point 85 to S6 centi- MARlIN ()VIQRLAUH.,g'iuttlesoluble With clifiieulty in cold \vatenbenzone andlig1'0ine,reaclily soluble in alcohol and other, and adapted for use asan anesthetic.

Witnesses:

\V. SPIELMEYER, PAULA E. MUnNon.

